Stereocontrolled Total Synthesis of (-)-Isocelorbicol and Its Elaboration to Natural Dihydro-β-agarofuran Esters

Tomoyo Mohri, Yusuke Takahashi, Eunsang Kwon, Shigefumi Kuwahara, Yusuke Ogura

Research output: Contribution to journalArticlepeer-review

Abstract

The first total synthesis of four naturally occurring dihydro-β-agarofuran esters has been accomplished via a highly stereocontrolled 14-step access to their common core triol, (-)-isocelorbicol. A semipinacol rearrangement of an epoxy alcohol to install a quaternary carbon, diastereoselective conjugate reduction of a spirocyclic butenolide for the establishment of a methyl-bearing chiral center, and ring-closing metathesis to construct the decalin ring system were exploited as the key steps for the high-yielding synthesis of (-)-isocelorbicol.

Original languageEnglish
Pages (from-to)9234-9238
Number of pages5
JournalOrganic letters
Volume22
Issue number23
DOIs
Publication statusPublished - 2020 Dec 4

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Stereocontrolled Total Synthesis of (-)-Isocelorbicol and Its Elaboration to Natural Dihydro-β-agarofuran Esters'. Together they form a unique fingerprint.

Cite this